Dean's Hell
by Kaybee331
Summary: I wanted to go into more detail of what i think Dean's time in Hell was like. This will be filled with torture of the body and mind.
1. Chapter 1

I own nothing, not Sam or Dean or any others that will appear. But if I did own Dean oh the fun we would have :)

Deans time in Hell was something we learned very little of. This is my idea of what he endured and as time went on how he was changed. This will for sure be graphic, violence and torture.

Dean had spent what seemed like a life time suspended in the nothingness. Meat hooks ripping his skin from his bones, fire dancing far too close for his comfort. If he had been living he would have sweated every pound from his body. The pain had been unbearable. He had screamed, begged and cried. He screamed out to Sammy, he prayed to God, anything to stop the pain. This did finally come to an end though. He was unsure his new torment was a relief of any sort. The hooks seemed to be a sort of a waiting room, like they were getting his paperwork in order or something. Perhaps they were sorting through his darkest fears and deciding what else would make him scream. His new waiting room was no bigger than 3x3 feet the ceiling rested right above his head. There was no once ounce of light. There was no pain but he was alone, beyond alone. He was able to sit on the floor, he curled his knees to his chest and laid his head on them. He was having an anxiety attack, he gasped for breath and his whole body shuddered uncontrollably. He felt like his chest was caving in and he couldn't stop tears from soaking his jeans. He wasn't sure if his body and lungs or even his jeans really existed anymore. Perhaps this was just how he perceived things to be. He never knew he could feel and act so weak, but who was here to witness it? Dean himself had no way of knowing how long he stayed in the closet like area but it had been a year. A year without hearing a sound except his own heart beating. A year without even a crack or slither of light. Of course in Hell there was no food or drink, he no longer had the need to relive himself. He just sat curled into a ball, a shaking, silent ball.

The day finally came when there was light, the wall to his room open. It was like there had always been a door there. A demon stood on the other side of the door. He had a human form. He was around Deans age, attractive with messy blond hair and large green eyes. He stood staring down at Dean. Disappoint almost seeped from him.

"You can't be the Dean Winchester, you sniveling, worthless dog. The stories that are told of you, this cannot be the man I have truly found." He said in disgust as he looked at the shocked shell of a man that was curled up on the floor. He surveyed him, Deans nails were all but gone from the time he had spent clawing at the walls, his face wet from tears and his eyes were beyond bloodshot. He looked like the light was burning his eyes. The man snickered, come boy it is time to begin your lessons.

Dean stood, the light was hard to take in, it had been so long since he had seen it. He followed the demon anything had to be better than his former cage. Little did he know he was so very wrong.

They entered a large white room, large harsh lights hung from the ceiling. The walls were almost made of glass, the floors white marble. There was a table in the middle of the room with straps, it looked like a mental ward. The demon began to speak again, his voice was unnerving.

"I am Alastair, I have many jobs but my most important, oh and favorite is to oversee torture. To teach it to be taken and given. I am sad to see you in such a sad state, I never intended you to break before I even began. It will really take the fun out of the game now won't it." Alastair snapped his fingers and tables of tools appeared. There must have been everything you could possibly cut or slice a human with laying there. There where a large assortment of whips and devices also.

Something inside Dean snapped back in place, though he took several steps back from the table and the tools his spirit began to flood back in. There was no way he would show this son of a bitch anything.

"Alastair is it? You know I am not so sure about this bed thing today. I mean you haven't even bought me dinner. How could you imply I am that sort of guy, not to mention I was never really into the S&M thing."

Alastair looked beyond delighted, perhaps this would be more fun than he thought. Dean planned to fight and yes he would lose, no matter what he would end up strapped to that table day after day. If the stories he had heard of the hunter were true, even when Dean was on the table he would have a world of fight in him. It would be fun to watch each day as that last bit of hope left his eyes. Of course there was more to this than that. Alastair had to make Dean step into the role of the torturer. For Alastair to receive his honors he had been tasked with forcing Dean to take up the knife. At first when he heard of Dean he had his doubts, but as soon as he opened the door to face him he knew there would be a time when he would break. It was just a matter of time and in Hell time was no issue.

Alastair took a step forward, reaching down and taking one of the whips in his hand. The whip was large and long, the end slimming down to a very fine stretch of leather. With his other hand he snapped his fingers, making any doors in the room vanish. Deans eyes seemed a bit panicked when he saw this. Actually Alastair had the power to snap and Dean would be bound on the table in less than a second. Not today though, today he would show Dean the hard way. He watched the hunter eye the tables filled with weapons, of course he was trying to see his best route to getting one. Alastair laughed.

"So sorry Dean-o that's not in the cards. Now you be a good boy and come have a seat on my table, perhaps I will go easy on you." Alastair smiled with malice as he spoke.

"I think I will stay vertical if it's all the same to you this is Hell nothing has been easy so far. I don't think trusting a Demon is going to get me any breaks buddy." Dean said as he backed himself into a corner. He knew he was going to lose, there was no escape and no where to hide. He just couldn't go willingly

Thanks so much for reading, I will get chapter two up as soon as I can! Please Reveiw I am always scared I am a bit too twisted.


	2. Chapter 2

I own neither Dean or Sam or any of the characters from Supernatural

There will be detailed torture of Dean in this part!

Dean and Alastair played a game of cat and mouse for what seemed an hour or hours. Dean would make his way closer to the table of instruments only to be pushed farther away from them. It all seemed so very pointless to Dean, he had seen the things Alastair could do by only snapping his fingers. He had no disillusions about the power the demon held. If Alastair wanted him on that table he would be there. The only thing that kept Dean fighting was the longer he fought the longer it prolonged one of those horrible tools from cutting into him.

Alastair was growing tired of the game though, with a quick flick of his wrist the whip snaked through the air and wrapped around Deans ankles. Another flick sent Dean crashing down on the hard marble floor.

"Ow! Was the really needed!" Dean barked from the floor.

"Really Dean, that you considered painful?" Alastair looked down at the scowling hunter. He would truly enjoy showing Dean what pain was.

Dean wasn't even sure how Alastair had put him there but now he was on the table. The cuffs placed around both wrists and ankles. He had not even an inch of wiggle room. The binds would not break, he was certain of that. Alastair was gone he was alone once more. Dread washed over him, he would be back. This absence he was sure was to allow Dean to build his fear or perhaps have a few more anxiety attacks. From his position he could see every sickening tool that Alastair would have at his disposal. Dean closed his eyes and tried to force himself to look away. It did no good, he turned back to the table and began to inspect. There were a dozen different knives, each one looked freshly sharpened. At least five whips, the basic one Alastair had wrapped around his ankles and then some with many tails at the end and shards of jagged glass attached. There were small tiny rods which had spear like tips. There were several small bottles, he couldn't read the chemical names but saw acid written in small print. Then there was a cork screw, why this was the tool that took Deans breath he was unsure. The devices on the other table seemed like small torches and other things, he wasn't sure he wanted to even know. He knew there would be no rescue, no Sammy or Bobby this time. This was going to happen, this was forever. Could he possibly detach himself, how bad would the pain be? He was starting to shake when Alastair returned. Dean quickly regained control, forcing his body to calm.

"Did you enjoy our game, you must know it was nothing more than a game. You can't win here. It's not in the cards, and never will be. Your in Hell Dean and by choice. When you made that little deal is this what you expected? Was your year with Sammy really worth this." Alastair gestured to the tables filled with tools. "Is Sammy worth all this, Dean?"

Deans voice was rough and strangled as he spoke. "Yes, he is worth it, it was worth it."

"Then we start." Alastair smiled at Dean and reached for the table. His first weapon of choice was a knife. It was simple, small and sharp. He walked over to Dean who had plastered a look of defiance on his face. Alastair knew it wouldn't take long to remove his smugness. First he trailed the knife gently down Deans jaw. "Ah perhaps there is too much cloth here for me." With a snap Dean was shirtless. The knife continued its travels down to Deans shoulder then to his chest. As he carefully, gently let the blade glide across his stomach he plunged it into his side. Dean bit back his scream but Alastair could see the pain on his face and the fear growing in his eyes. Alastair turned back to the table and picked up a larger blade. He began the same teasing until he ripped through Deans jeans and firmly planted the knife into his thigh. This time Dean could not stop the scream from escaping. Alastair kept going until each of the blades were embedded into his victim. "The wonderful thing about Hell Dean is you can't die. The pain won't stop until I allow it to." Alastair began to chose his next toy. He picked up one of the small metal spikes. He walked over to Dean and grabbed his hand and one by one began to drive the spikes under his nails.

Dean had not been able to control himself enough to even speak. He had screamed though. He had no idea he could scream so long and loud. The spikes going under his nails were beyond any pain he had ever felt. He screamed and he jerked, his body convulsing making the knives send horrid pain through him. He had lost all control, there was no way to calm himself at this point. The last of his fingernails took in a final spike. Dean's screams never stopping. His only shard of self he had left was he had not begged. Begging would do nothing but cause Alastair more triumph. Then he felt Alastair's touch on his toe. He felt the spike begin to slice under the nail, he leg convulsed in such a way that he heard his bone break. Then he heard laughter. Alastair finished with his toes and then stood back to survey his work. Dean was still screaming, knives protruding from him everywhere and the small spikes out of each nail. This would be well enough for their first day. He would let his stew in his pain for days before taking it away. Alastair left him but there was nowhere in Hell Deans screams could not be heard.

So there is chapter two, truly I had some more gruesome ideas but I couldn't bear to do it to Dean. Perhaps later on. Please review!


	3. Chapter 3

I do not own Dean or Sam Or any of the characters from Supernatural.

I am having fun writing this one though a bit apprehensive about how far I can go on torture. This is only my second fanfic so far so I am still learning as I go. Please review for me!

Dean was back in his small closet like room. Back to the deafening silence and pitch black. He had to admit after the torture he had endured the the dark cell was somewhat comforting. He had stayed on the table for what seemed like forever. His screams had gone on for days, they were only silenced by the fact that he became unable to choke out any noise. The rods in his nails were beyond any pain he had ever felt. The knives and his broken leg were almost unnoticeable to that pain. In fact by the time Alastair returned he had broken his right wrist too. Alastair came to him and laughed at the state he was in. He healed him and snapped him back to his cell. Dean wasn't sure how long he had been back, all he knew was for the minute he wasn't in pain. Of course Alastair would return, it would begin again. Was this despair truly his existence now? He thought over what Alastair had asked, was it worth it. That year with Sam had been good. He wouldn't trade it for anything. Sam would always be worth it. He knew without a doubt Sammy was working on freeing him. They had tried to stop the whole thing but that had become impossible, but if there was any way to get him out Sammy and Bobby would find it. He would hold onto that hope and let nothing take it away. He had to hold some faith, if there was a hell there was a heaven. If there was a devil then there is a God. He would pray, pray to anyone who could hear him because that is all he can do.

When the slither of light appeared once again Dean went rigid. The man standing before him was once again Alastair. Dean pushed back all the fear that was so close to spilling out.

"Ah Alastair, what's on the menu today? Do we have time for breakfast first?" Dean said with a smirk. He wouldn't let him see the fear he was fighting so hard.

"Of course I wouldn't deprived you." Alastair said as once again he snapped his fingers. They were in a diner, a real diner with waitresses,cokes and grease. Alastair handed Dean a menu.

Dean sat smelling the food, this was his first chance of eating since he died. You didn't eat in hell, it wasn't for lack of hunger. You were starving at all times, but there was never food. Of course he couldn't starve to death, and you didn't waste away so you were just hungry. There was no way this was real though. He swore to himself he would send some money to the starving kids in Africa if he got out. There was no way he would allow himself to think this was real, Alastair wouldn't let him eat, would he?

"So what is the trick, you were shoving rods under my nails a few days ago and now your going to wine and dine me?" Dean asked with trepidation in his voice. He had prepared himself to be smug and defiant but this, he had no idea what to make of it.

"Dean order your food, we need time to talk. If you don't want it, I am sure we can talk while I work." He said as he eyed Dean.

The waitress came to their table, she was a demon that was for sure. Dean quickly ordered a bacon cheese burger, fries a shake and a coke. The food was there before he even finished speaking. The smells of his favorites were making him dizzy. He grabbed the burger and took a bite. It was real, he pushed back the tears of relief that wanted to come.

"Now Dean, I want to make you a offer. You don't have to go through all of this pain, I can make it stop. You can eat, I will even allow you sleep. Best of all you won't find yourself back on my table." He said while he watched him eat.

Dean put his burger back down and met Alastair's eyes. "How?"

"You become my apprentice, I teach you in the ways of torture. You chose to pick up the knife and I will lay mine down." Alastair laid his offer out.

"No, you sick son of a bitch. You think I am going to carve people up the way you do. Make them scream. I will never work for you, I am not evil. I am not one of you." Dean responded as he glared at Alastair.

"If that is your answer, then so be it." Once again Alastair snapped, the food in front of Dean became molded and rotten and maggots spilled from the meat that just moments before had offered such hope. The coke turned to blood, the fries worms and the shake became a spoiled putrid substance. Dean immediately began to retch, throwing up the little bit he had consumed. Then the diner was gone and he was bound back to the table. Dean was back in the room and he was alone. It had all been a trick, of course it had. Deep inside he knew there was no chance he could really be given any mercy. This was Hell after all. Dean refused to allow himself to look at the table of tools to his side. He didn't want to know what would come next.

Alastair returned to the room and began working quickly, he spoke very little. He laughed though, every scream that he brought out of Dean was a small victory. This time he began with a peeler, he sliced the skin from Dean's body. There was no way for Dean to calm himself as the blade took long strips of his flesh and they dropped to the floor. He tried to take himself back to some of the best moments he had. He thought of Sammy and him burning down that field on the fourth of July. The complete carefree happiness they shared that night. He had given Sammy something John was unable to, a moment to be a kid. If he could just stay in this moment, just for a few minutes perhaps the pain would lessen. Once Alastair had completely skinned his chest he laid the tool down. Dean dared not open his eyes. At least he wouldn't know what was next. He heard something being lifted, then the air was cut, a slicing whistling sound. A whip ripped across his shredded chest. This explosion of pain took Dean by surprise. He jerked both wrists in response, a broken scream escaping his lips. This was one of the whips which had the shards of glass at the end and as it struck it grabbed hunks of already exposed flesh and ripped them free. The assault kept going till his whole body, arms and legs looked as open and raw as his chest. If he had dared to look he would see he was nothing but a mangled pile of flesh. Ribs were exposed, there was more blood on the floor than in him. The walls were spattered with bits and pieces of flesh, bone and blood. Dean was sobbing, screaming and gasping for air. The glass had nicked his lung and it was partially collapsed. Once again you don't die in Hell, so he laid there as he was and how he would until Alastair healed him again.

"Dean, I will ask you once again today. Do you want this to stop. All you have to do is join me." Alastair asked as he walked around inspecting his work.

Dean couldn't speak, but he shook his head.

"Fine then, I will send you back to your room. Tomorrow we shall play again." Alastair smiled as he snapped his fingers.

Dean was healed and back in the cell once again. This time he cried, he wasn't sure the tears would stop. He screamed into the dark for Sammy and fell to his knees. This is how it went on for Dean for the next thirty years. He assumed it would always be this way, till the day that changed it all.


	4. Chapter 4

I do not own Dean or Sam or any of the Supernatural characters

Thanks so much for reading this fanfic! I have been working hard to show what I feel went down in hell. I hope you guys are enjoying it!

It had been thirty years, Dean himself had no ability to keep track of time. Hell wasn't like Earth, the sun rises and sets and another day passes by. No, there was endless amounts of time spent in the white room he never knew how long he was there. Then he was zapped back to his cell. Perhaps that was his night and day, the darkness of the cell was the most peace he was able to obtain and then the harsh blinding light in the white torture room. Either way none of that allowed him to track time. If it were true, thirty years had gone by, Sammy was in his fifty's if still alive. Hell, Bobby was probably dead. The chance that Sammy was going to come hobbling in to save him now was almost gone. He would always hold on to whatever hope was still there. The sessions had become lighter there for awhile, Alastair's new tactic to get him to say yes. Now though they were more brutal than ever. Alastair's new trick was to use a bread knife to cut his limbs down to the bones and then sever them all. Maybe that wasn't the worse, there were the days he burnt all the flesh from his body with a very small torch. It took hours and the pain never stopped. Ah lets not forget when he would turn him upside down and drown him in a bucket. You would assume this would be the least painful of the all, but no the pain of your lungs about to burst from the pressure and the horrible feel of swallowing the water into them. It doesn't stop when you can't actually die. No longer did Alastair allow Dean to pretend he had a chance of avoiding the table, he was snapped straight into the binds. Alastair was very clear that Dean was to know he had nothing, no power and no chance to fight. Yet, day after day the question was asked and day after day Dean said no. He wouldn't join Alastair.

The last session had been the most painful to date though. This had been a lesson in the tools of the trade. All the tools that were used had been used in Deans hunts. He saw all his various handguns, shotguns, stakes, salt, gasoline, rifles and knives. It was their basic go to weapon kit they kept in the impala. Alastair had used every one of those weapons in some way. The rock salt gun was hell when it was hitting an already carved and shot up body. The gasoline though, when he was done with the hours of torment he picked up the can and began to douse Dean in gas. He left him burning for hours, the sounds that escaped Dean were inhuman. This had been the worse and Dean almost wanted to say yes. If he was going to be here forever why not have a bit of a break. He refused though, he swore that as long as there was a grain of hope he wouldn't say yes. If he gave in and played Alastair's game then somehow got back topside how could he ever face anyone. He had to endure and wait for these moments, the ones where he was healed and alone. He had never been a fan of being alone before but now it was his only time he was safe.

The slither of light appeared, Dean dropped his head in his hands. How could he be starting again so fast.

"Dean, thank God I found you!"

Dean's head snapped up, he was looking at Sammy. The same Sammy he had left behind, his brothers hand was outstretched to him. Great, he thought, now I am seeing things. He lowered his head back down and wished the vision away. Sammy dropped to his knees beside him, and placed his hand on his shoulder. He pulled him into a tight embrace. Emotions showing glistening in his eyes.

"Dean I am real, I am here but we have to get moving. Bobby can only hold the door open for a very short time." Sam said rather frantically.

"Right, so if your real why are you the same as when I left? It's been years and years there is no way you look like this." Dean said as he got to his feet.

"Dean I am not sure what you mean, it's been three months. We can discuss this when we are out." He grabbed Dean by the arm and dragged him from his cell.

Deans mind was racing, Sam felt real, looked real he could even smell him. His throat let a sob escape and tears began to fall. Could he really be getting out? He let Sammy pull him along. He was in total shock, how many times had he prayed and begged to God and Sammy to save him. Could they really evade Alastair and get out? He had never wanted anything so much,

"How did you guys do it? How do you get into Hell and still be able to walk out?" He asked as Sammy pulled him along.

"It's really complicated, an old spell took forever to find it, but you know Bobby if it's there he will find it at some point." Sam replied.

As they ran Dean could see a shimmering like tear up ahead, this must be it. This is how Sammy got in. Deans emotions were everywhere, complete fear that they would be stopped before they could get out. Then there was the happiness, this was a feeling he had forgotten he could even feel. He knew he had to get to the other side to know it was really safe to feel that. It seemed to take forever even though it was only seconds but they reached the shimmering portal. Sam reached his arms in and then pulled himself and Dean through. Just as he was putting his last leg through the world tilted and shifted. Then the harsh lights of the torture room flooded his eyes. He was back on the table, wrists and ankles bound, and somewhere Alastair was laughing.

Dean screamed and cursed at Alastair. "Where the fuck is Sammy, what did you do with him!?"

"Oh Dean don't you see? Sammy wasn't real you have been holding that mustard seed of hope for sometime now. I gave you a glimpse of what will never be. There are no age old spells that let you enter Hell and pull someone out. God isn't going to swoop in here either. Lucifer is very clear on those details, what is his remains his. No your brother has moved on with his life and so has the old man Bobby. Nobody is breaking down Hell to get to you." With that being said Alastair left him with his thoughts.

Dean broke, the tears came without his notice. His hope began to seep away. He knew everything that had been said was more true than not. The chance to hug his brother, the chance that he would step through that portal and all the torments of Hell would be gone, it was too much to be put in front of him. This was his new life, he had to face that. He thought about all the promises made by Alastair. He would be able to sleep and eat and no longer would he face the table. Maybe that was all there was here. That one thing could be his hope. He didn't want to hurt people but most were here for some reason. The amount of people who made deals to save family had to be pretty slim. He killed the evil up top, he could slice into it down here. Sure there was a nagging voice screaming at him to hold out. He would have to turn that voice off for now. He couldn't escape but he could change his fate. He looked over at Alastair who had reappeared and was entering the room.

"Fine I'm in"


End file.
